You Are What You Make: Founders Become Their Startups

He was hired by PayPal at age 22 into a stress-free role. Then he moved to LinkedIn where he had a slightly more "exasperating" but still not-so-stressful job.

When he founded a company, Circle of Moms, everything changed.

He changed.

He and his startup became, essentially, the same thing.

"LinkedIn’s successes were nice but hardly life-affirming; its failures made me roll my eyes but not search my soul," Greenfield explains on FounderDating. "When you’re a founder, your company defines you. That means that your company’s daily ups and downs become your personal ups and downs; that’s a big adjustment."

Greenfield says the hardest thing for him to learn while founding a company was how to constantly put himself up for public scrutiny.

"As a techie individual contributor in a larger company, I could go to work everyday and execute 99% predictably," Greenfield writes. "As a founder, I had to find ways to plead my case over and over — to employees, investors, candidates, advertisers, users — and I got rejected a lot. For an introvert, the amount of pleading and subsequent rejection came as quite a shock.

"As a founder, you need to be prepared for this sort of rejection. It should affect you: if it doesn’t, it means you don’t care enough and should be doing something else."